A Simple, Effective Boron-Halide Ethoxylation Catalyst

A Simple, Effective Boron-Halide Ethoxylation Catalyst

Boron esters B(OR)3, readily derived from boric acid and alcohols, combine with iodide or bromide to catalyze the ethoxylation of alcohols and phenols, giving good rates and narrow product distributions. The combined action of a weak electrophile [B(OR)3] and a weak nucleophile (halide) allows for t...

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Veröffentlicht in:Advanced synthesis & catalysis 2010-03, Vol.352 (5), p.821-826
1. Verfasser: Moloy, Kenneth G.
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols
Boric acids
boron
Esters
Ethoxylation
ethylene oxide
halides
Iodides
Nucleophiles
Phenols
ring-opening polymerization
Synthesis
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Beschreibung
Zusammenfassung:Boron esters B(OR)3, readily derived from boric acid and alcohols, combine with iodide or bromide to catalyze the ethoxylation of alcohols and phenols, giving good rates and narrow product distributions. The combined action of a weak electrophile [B(OR)3] and a weak nucleophile (halide) allows for the ethoxylation of base‐sensitive alcohols. Experiment suggests a new mechanism for this commercially important reaction proceeding through key β‐haloalkoxy intermediates.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201000004